143123-38-0Relevant articles and documents
Molecular Rods: Synthesis and Properties
Zimmerman, Howard E.,King, Russell K.,Meinhardt, Michael B.
, p. 5484 - 5492 (1992)
Our earlier synthetic methodology affording bicyclooctyl -rod and -rod systems proved inadequate for -rods.New synthetic approaches were developed, and - and -rod molecules were obtained.Sodium-potassium coupling was employed to afford the longer rod units.A radical anion approach gave lower yields.Hybrid rods with aromatic rings interposed were also synthesized.Rods of 9.2-, 9.7-, 13.4-, 13.9-, and 18.2-Angstroem length were included in this study.Consideration of rod chirality suggests each bicyclooctane rod unit to be stereogenic, either P (clockwise) or M (anticlockwise).Thus, in a -rod there are enantiomers and in a -rod there are diastereomers.Molecular mechanics treatment of rod stereoisomerization was carried out.Interconversion of enantiomers of the -rod and diastereomers of the -rods should be very rapid at room temperature.X-ray analysis of the 4,4'-dimethoxy--rod reveals an achiral conformation.AM1 quantum mechanics computations were carried out on -rod radical cations and bridgehead cations.
